3-Tert-butyl-isoxazole-5-carboxylic acid [3-nitro-4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide → 2-(3-tert-butyl-isoxazol-5-yl)-7-trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine

HRID 570225노트

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HRID 570225 반응식
[N+:1]([C:4]1[C:5]([NH:24][C:25]([C:27]2[O:31][N:30]=[C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:28]=2)=O)=[N:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])([O-])=O>CC(O)=O.[Fe]>[C:32]([C:29]1[CH:28]=[C:27]([C:25]2[NH:1][C:4]3[C:5]([N:24]=2)=[N:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:21])([F:23])[F:22])=[CH:8][C:9]=3[C:10]([F:13])([F:12])[F:11])[O:31][N:30]=1)([CH3:33])([CH3:35])[CH3:34]

참가 물질

4

반응물 1

HCID 866574113-Tert-butyl-isoxazole-5-carboxylic acid [3-nitro-4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide

생성물 1

HCID 1360731612-(3-tert-butyl-isoxazol-5-yl)-7-trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

A solution of 3-tert-butyl-isoxazole-5-carboxylic acid [3-nitro-4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide (14.6 mg, 0.029 mmol, prepared as described in STEP E above) in AcOH (3 mL) was treated with iron powder (8.12 mg, 0.145 mmol), and the resulting mixture was stirred at 100° C. for 2 h and concentrated in vacuo. The residue was taken up in saturated aqueous NaHCO3 (30 mL) and extracted twice with EtOAc (25 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 4-g SEPRA Si 50 SPE column (Flow rate=10 mL/min; Eluent=EtOAc-hexanes, 1:99 for 10 min, then 1:99 to 1:4 over 40 min) to yield 2-(3-tert-butyl-isoxazol-5-yl)-7-trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine as a white solid. 1H-NMR (400 MHz, CD3OD) δ: 7.77 (d, J=7.6 Hz, 1H), 7.63-7.69 (m, 1H), 7.58-7.62 (m, 2H), 7.52-7.58 (m, 1H), 7.26 (s, 1H), 1.33 (s, 9H). Mass Spectrum (LCMS, APCI pos.): Calculated for C21H16N4OF6: 455.1 (M+H); Measured: 455.1.

후처리

  1. concentrationconcentrated in vacuo
  2. extractionextracted twice with EtOAc (25 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a 4-g SEPRA Si 50 SPE column (Flow rate=10 mL/min
  6. waitEluent=EtOAc-hexanes, 1:99 for 10 min

출처 및 근거

ORD 기록
ord-b2a962fd69724c269701867d403667ac
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023846B2

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